Two new sulfated steroidal glycosides, imbricatoside A (I) and imbricatoside B (II), which inhibited cell division of fertilized sea urchin eggs, were isolated from the aq. exts. of whole bodies of the starfish D. imbricata. They contain the same disaccharide chain, i.e., 2,4-di-O-methyl-β-D-quinovopyranosyl-(1→2)-5-O-sulfate-β-D-fucopyranosyl, which is linked to C-24 of 5α-cholestane-3β,4β,6α,7α,8,15β,24-heptaol and 5α-cholestane-3β,6α,7α,8,15β,24-hexaol aglycons. The exts. also contained 6 new polyhydroxysteroids, to which structures were assigned. (22E,24R)-5α-Cholest-22-ene-3β,6α,8,15β,24-pentaol showed strong antifungal activity and also inhibited cell division of fertilized sea urchin eggs.
Starfish saponins, part 43. Structures of two new sulfated steroidal fucofuranosides (imbricatosides A and B) and six new polyhydroxysteroids from the starfish Dermasterias imbricata
BRUNO, Ines;RICCIO, Raffaele
1990-01-01
Abstract
Two new sulfated steroidal glycosides, imbricatoside A (I) and imbricatoside B (II), which inhibited cell division of fertilized sea urchin eggs, were isolated from the aq. exts. of whole bodies of the starfish D. imbricata. They contain the same disaccharide chain, i.e., 2,4-di-O-methyl-β-D-quinovopyranosyl-(1→2)-5-O-sulfate-β-D-fucopyranosyl, which is linked to C-24 of 5α-cholestane-3β,4β,6α,7α,8,15β,24-heptaol and 5α-cholestane-3β,6α,7α,8,15β,24-hexaol aglycons. The exts. also contained 6 new polyhydroxysteroids, to which structures were assigned. (22E,24R)-5α-Cholest-22-ene-3β,6α,8,15β,24-pentaol showed strong antifungal activity and also inhibited cell division of fertilized sea urchin eggs.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
